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Because I’ve become rather well known for my Maxims (you’ll find more on how they came to be here), and because I will be referring to them so regularly here, it’s only fitting that I should include the complete list (as it currently stands) among my earliest of posts in this forum.

Whatever successes I’ve had in life have come mainly from following the below maxims (albeit far less consciously in my early years). And whatever failures I’ve experienced have usually come from ignoring them.

Consequently, they are intended to be applied by rote without much second-guessing or rationalizing. For this reason, they are written emphatically as if they are absolutes. Yes, yes, I’m sure that you can think of instances where they are wrong or don’t apply, but I doubt you’ll find very many cases where they are wrong or don’t apply, and that matters to your life very much.  Don’t let the perfect be the enemy of the great.

Few of The Maxims are original to me. Everything I’ve learned, I’ve learned from someone else—my loves, my family, Nassim Taleb, Ray Kurzweil, Peter Thiel, Steve Jobs, Brene Brown, Robert Schuller, and so many more.

And now The Maxims:


Always be right when it matters. It matters most when being wrong is potentially catastrophic. For instance, never allow yourself to mistake a bear for a rock.

The price of being right when it matters is frequently being wrong when it doesn’t (i.e., often mistaking rocks for bears). Forgive yourself these harmless errors and ignore those who would shame you for them.

Never make decisions based on how likely something is to work but instead based on the cost of it not working. When the price of failure is high, having high odds of success is irrelevant, so do not proceed. But when the cost of loss is low, low odds of success are irrelevant, so leap!

Constantly look for opportunities to risk a little for a lot—opportunities where the gain if you are right far exceeds the loss if you are wrong and the odds are reasonably in your favor.

Never rely on the guidance of subject matter experts when making risk-based decisions (except to understand the nature of the relevant risks better).

Opportunity costs matter when the cost of being wrong is low. When the cost of being wrong is high, forget about opportunity costs. Far better suffer the opportunity cost of maintaining a 90-day emergency fund that you never need than to need it and not have it.

When the selfish incentive to defect from an alliance or cartel is great, defections are all but assured (and especially among rivals). In these circumstances, never favor outcomes dependent upon the coalition holding together indefinitely.

Good decisions are made at the margin. Sunk costs are irrelevant to how you should proceed. Forget about them when planning for the future.

When information is imperfect (and it almost always is), assessing risk is complex. In such cases, make choices that preserve optionality (that is, keep the most future options open to you). Well, unless you have to lie to do it.

Nothing good happens after midnight. Be home before then.

Never make permanent decisions in response to temporary circumstances. So, among other things, never make permanent decisions in a triggered state.

When choosing between two superficially appealing opportunities, go with the one that affords good luck more opportunity to play out.

Judge the wisdom of past decisions by how well they accounted for the risks and information available to you (after diligent inquiry when possible) when the decision was made and not by their ultimate outcomes.


Never mistake a liquidity crisis for a solvency crisis or vice versa. The distinction is important and impacts how to hedge your risk.

That which can’t continue won’t continue no matter how popular or ubiquitous it has become, though it can persist for far longer than you think. Find ways to protect yourself against its eventual collapse. Or better, to safely exploit its eventual collapse.

Seek opportunities to exploit the long-term success of antifragile systems, especially those benefiting from network effects.

Even fragile systems can persist far longer than you expect, and markets can stay irrational far longer than you can stay solvent. Avoid leverage, stay liquid, and be patient.

Never listen to economists or finance people regarding the potential value (or lack thereof) of emerging technologies. Consider only the opinions of tech people about such matters.

Buy when there’s blood in the streets, even if it’s your own.


You will never become successful or happy by diminishing those who are.

How you do anything is how you do everything. It’s the little habits that count. For instance, showing up for work on time each day will significantly impact your future success and happiness more than which job you choose or the college you attended (or didn’t).

Success is far more random than most people believe. Great innovations and outcomes are almost always a fortuitous result of luck or relentless tinkering and not the result of perfectly executing some preconceived plan.

Fail early, fail often. “If you’re not embarrassed by the first version of your product, you’ve launched too late.” Good and done is nearly always better than perfect and not.

Beginning something is half done. Just start!

Never judge your past successes or the wisdom of some past decision by the results you achieved but rather by the loss you would have sustained had you failed. Only idiots ever win at Russian roulette.

You become like those with whom you surround yourself. Choose wisely.

Never interrupt your enemy when he is making a mistake.


Talk is cheap. Disregard the opinions of those with no chip in the game, especially coffee house intellectuals and talking head "experts." (Note to self: Disregarding them does not mean reflexively assuming that everything they say is wrong because sometimes they are right. It simply means not giving their opinions any consideration at all).

Wisdom consists of the development and application of effective and rational biases.  The more your particular biases map well to reality, the more “wise” you are. (The opposite is also true).

The unbiased person is a fool.  Seek not to be unbiased, seek to be rationally biased.   

Unbiased opinions are way overrated. A biased opinion from someone who necessarily loses something that he already has if he is wrong is far superior to an impartial opinion from someone who loses nothing.

Correlation does not necessarily mean causation. It usually doesn’t. Never, ever forget it.

Occam’s Razor is usually correct, and therefore most conspiracy theories are generally wrong. Beware of any offered explanation with multiple layers of inherent, unverified assumptions.

Nothing in biology and little in psychology or culture makes sense except in the light of evolution. Deny evolution, and you cannot see clearly.

Always seek to negate your hypothesis, never to confirm it. No amount of corroborating evidence will make something certainly true. But negating it makes it conclusively false. Negate, and then you know.

An argument that you would not accept from your opponent is not worth making. And if you make it anyway, then you’re just trolling or engaging in mental masturbation (stroking your narrative) rather than attempting to discern truth or to persuade your opponent.

Never depend on or vouch for the judgment of those who are devoted to conspiracies.

Trust the least those who trust the least. Trustworthy people are most often trusting people.

What can be asserted without evidence can be dismissed without evidence.

Game theory incentives will win out. No alliance or conspiracy is immune from defections when the incentive to defect is real and robust.

Never accept extraordinary claims without extraordinary evidence. Extraordinary evidence will not suffer from selection or other improper biases and will not be rooted in fallacious reasoning.

Human culture and the arc of human history result from human nature (core drives and motivations) being channeled this way or that by new, innovative technologies. Human nature changes very little over time, but change the tech and you change the world.

Judge a person’s priorities not by their words or even their tears but by their calendar and checkbook (where they spend their time and money).


The triggers are the guides. If it hurts or offends, it’s because it's true or feared to be true. Never pretend otherwise.

Offense is always taken, never given. If you are offended, it’s because you are tender.

Except for tech, there is nothing new under the sun. Any contention that humans' core motives and drives are different today than in the distant past is likely bullshit.

Ensure that all transactions and relationships are win/win both at initiation and as things evolve. Win/lose or lose/win deals or relationships always devolve into lose/lose. Make it win/win or no deal.

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After the tipping point (third doubling from 1 percent), exponential growth patterns in technology and biology don’t just stop of their own accord until acted upon by some sufficiently capable outside force or until saturation is reached.

Network effects are very antifragile. Trust them early (but protect your downside, at least until the tipping point).


Self-care is not optional.

Take all things in moderation.

Be always content but never satisfied.

Entitlement is the opposite of gratitude. Life owes you nothing—governments, people, and “society” even less.

Do your dharma and detach from outcomes.

There are no solutions, only trade-offs. Everything in life comes at a price, most commonly a trade-off. Accepting the reality of trade-offs results in gratitude and contentment, and denying or resisting them results in resentment and misery.

Happiness is a result of making good trade-off decisions. You can’t give the meaningful things in life an unequivocal “yes” without giving most others an absolute “no.” To be happy, you must say “no.” A lot. Even to “good” things.

Live where the rest of the world vacations. 🇵🇷 

Inspiration results from acting with devotion.  If you wait to be inspired before acting/devoting, you'll be waiting a very long time.  If you would be inspired, devote!

Most people will choose delusion over uncertainty. Don’t be like most people! Use the maxims to embrace and manage uncertainty and prevent delusion.

People prone to let the perfect be the enemy of the good are both ineffective and miserable/resentful. Pure greatness does not exist. All progress is incremental and to be celebrated even in flawed persons.

Disable all social media and email notifications.

There is no fixing a problem that does not exist.

Do no drugs that are physically addictive or subject to overdosing.

Never drink, smoke or do drugs alone.


All growth happens in the context of relationships. 

Don’t do to others things that you’d not want done to you (well, unless they request it or consent to it).

There is no real relationship without brutal honesty.  

Brutal honesty is far better than well-intended deceit.  People can forgive and forget temporary meanness if rooted in truth, but a lie does everlasting damage.  

Many people want you to lie to them.  Don’t.  

People don’t leave something (even usually very bad things) for nothing.  This explains many abusive relationships.  

The smeller is the likely feller.  The first to complain should be the first to be suspected.  

People change.  But seldom.  And almost never in the way you hope.  (No ladies, he won’t change after you have his baby, at least not the way you’re hoping)

Take nothing personally.  It’s never really about you.

Never deny someone a favor when it costs you nothing. 

People seek to connect via compliments.  To reject or deflect a compliment is to reject or deflect connection.  Saying “thank you” or “I’m grateful”, and meaning it, is therefore the only appropriate response to any compliment.  

Being respected and disdained are two sides of the same coin. It’s impossible to gain the respect of some without offending others.  If you have genuine admirers then you will also have genuine detractors.  And if you think you have neither, then you’re just pandering.

If you can’t handle angering or disappointing others, then be resigned to a life of mediocrity and angst.  

When you are wrong or make a mistake, own it, apologize for it, mean it, and learn from it.  Then move on.  

Never trust or attempt to aid a narcissist.  You won’t change or help them, and they will screw you.  

People generally live up to your expectations of them.  Expect the best (except from narcissists). 

People are never trustworthy until you trust them. 

All romantic relationships (and most others too) are transactional in nature.  Be open, honest and transparent about that fact so as to avoid becoming manipulative, resentful and/or passive-aggressive.  


Focus your attention consistently on things that you can directly influence.

If the solution to your personal problem involves you changing others people’s minds or behaviors rather than you changing your’s, then its no solution at all. 

Blessed are the shameless, for they shall not be shamed.  

Properly managed, there’s no such thing as bad publicity.

Never confound culpability and responsibility.  You may not be to blame, but you are always responsible. 

We change people’s values not by persuading them but by finding a deeper value behind the one we seek to change and appealing to it.


Business is relationships.

If you’re going to take the risk of being an entrepreneur, at least build a business that will produce recurring income.  

If you’re going to take the risk of being an entrepreneur, at least build a business where your revenue stream is secure by your client’s assets.

What gets measured gets done. Success comes from tracking and reporting.  

Exceptional performers resent a boss tolerating mediocre teammates, and mediocre teammates resent exceptional performers.  A boss must choose sides.  Side with the exceptional ones.  

When hiring, reliability is twice as important as intelligence, intelligence is twice as important as social skills, and social skills are twice as important as ambition.  Except for narcissists (never hire one).


Never give oral interviews to print journalists.  Agree to written interviews or unedited recordings only.   

Have no secrets (except for your crypto keys).


A moral principle or ideal asserted in defiance of game theory will ultimately achieve its very opposite.  

You can’t successfully improve the morality within a Nash Equilibrium situation without first changing the underlying game theory dynamics that created the equilibrium, and attempting to do so will only result in more of the morally objectionable thing.

Never hate others for self-interested behaviors that you (or your tribe) would adopt under the same circumstances.  


Few things worthwhile come easily, not even love.  

What you resist persists!  Don’t resist what you fear or hate.  Subvert it through innovation instead.

Feelings are just feelings.  They are not problems until we act on them before getting to the bottom of them. 


[If you want to think and see more clearly; discern more accurately; predict more reliably and live, love, and understand yourself and the world more fully; or if you just want to watch people who do; then please continue to follow me here.]